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Synthesis and spectroscopic properties of chiral bornane[2,3-b]pyrazino-fused [30]trithiadodecaazahexaphyrins

IRLoN, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russia

Department of Fine Organic Synthesis, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

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Olga N. Trukhina

Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

IMDEA Nanoscience, Faraday 9, 28049 Madrid, Spain

Corresponding author.

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M. Salomé Rodríguez-Morgade

Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

SPP full member in good standing.

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Mikhail K. Islyaikin

IRLoN, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russia

Department of Fine Organic Synthesis, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

Corresponding author.

SPP full member in good standing.

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Oscar I. Koifman

IRLoN, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russia

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, and

Tomas Torres

IRLoN, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russia

Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain

IMDEA Nanoscience, Faraday 9, 28049 Madrid, Spain

Corresponding author.

SPP full member in good standing.

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https://doi.org/10.1142/S1088424614500771Cited by:11 (Source: Crossref)

Abstract

First chiral bornane[2,3-b]pyrazino-fused [30]trithiadodecaazahexaphyrins were prepared by a crossover condensation of R-(+)- or S-(–)-bornane[2′,3′-b]-2,3-dicyanopyrazine and 2,5-diamino-1,3,4-thiadiazole using two different methods. R-(+)- and S-(–)-enantiomers were characterized by their optical rotations and circular dichroism spectra, showing a mirror image relationship with respect to [θ] = 0. Regioisomers with C₁ and C₃ symmetry of R-(+)-[30]trithiadodecaazahexaphyrin have been separated using HPLC CHIRALPACK IC analytical column, allowing their unambiguous identification and characterization.

Dedicated to Professor Nagao Kobayashi on the occasion of his 65th birthday

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